CA1165324A - 1-aryloxy-3-alkylamino-propan-2-ols, et methodes pour les preparer - Google Patents

1-aryloxy-3-alkylamino-propan-2-ols, et methodes pour les preparer

Info

Publication number: CA1165324A
Authority: CA; Canada
Prior art keywords: group; tert; cyano; process according; propan
Prior art date: 1981-08-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000408021A

Other languages

English (en)

Inventor

Herbert Koppe

Werner Kummer

Helmut Stahle

Gojko Muacevic

Werner Traunecker

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim International GmbH

Original Assignee

Boehringer Ingelheim International GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-08-26

Filing date

1982-07-26

Publication date

1984-04-10

1982-07-26 Application filed by Boehringer Ingelheim International GmbH filed Critical Boehringer Ingelheim International GmbH

1984-04-10 Application granted granted Critical

1984-04-10 Publication of CA1165324A publication Critical patent/CA1165324A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 19
238000002360 preparation method Methods 0.000 title description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
125000002252 acyl group Chemical group 0.000 claims abstract description 6
125000004423 acyloxy group Chemical group 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
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125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 23
-1 alkixy Chemical group 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 13
QOBAXXQQFJJPAA-UHFFFAOYSA-N 1-(butylamino)propan-2-ol Chemical compound CCCCNCC(C)O QOBAXXQQFJJPAA-UHFFFAOYSA-N 0.000 claims description 7
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GCUUFJGPPZFQMD-UHFFFAOYSA-N n-[4-(3-chloro-2-hydroxypropoxy)-3-cyanophenyl]cyclobutanecarboxamide Chemical compound C1=C(C#N)C(OCC(CCl)O)=CC=C1NC(=O)C1CCC1 GCUUFJGPPZFQMD-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229940075065 polyvinyl acetate Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000004208 shellac Substances 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229930002534 steroid glycoside Natural products 0.000 description 1
150000008143 steroidal glycosides Chemical class 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000011282 treatment Methods 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Cardiology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Fats And Perfumes (AREA)
Medicinal Preparation (AREA)
Pyrrole Compounds (AREA)
Saccharide Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Seasonings (AREA)

CA000408021A 1981-08-26 1982-07-26 1-aryloxy-3-alkylamino-propan-2-ols, et methodes pour les preparer Expired CA1165324A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP3133678.7		1981-08-26
DE19813133678 DE3133678A1 (de)	1981-08-26	1981-08-26	Neue l-aryloxy-3-alkylamino-2-propanole und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
CA1165324A true CA1165324A (fr)	1984-04-10

Family

ID=6140122

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000408021A Expired CA1165324A (fr)	1981-08-26	1982-07-26	1-aryloxy-3-alkylamino-propan-2-ols, et methodes pour les preparer

Country Status (19)

Country	Link
US (1)	US4442120A (fr)
EP (1)	EP0073016B1 (fr)
JP (1)	JPS5859957A (fr)
KR (1)	KR890000620B1 (fr)
AT (1)	ATE16700T1 (fr)
AU (1)	AU558338B2 (fr)
CA (1)	CA1165324A (fr)
DE (2)	DE3133678A1 (fr)
DK (1)	DK380482A (fr)
ES (3)	ES515245A0 (fr)
FI (1)	FI75150C (fr)
GR (1)	GR77606B (fr)
IE (1)	IE54224B1 (fr)
IL (1)	IL66633A (fr)
NO (1)	NO152603C (fr)
NZ (1)	NZ201716A (fr)
PH (1)	PH19705A (fr)
PT (1)	PT75458A (fr)
ZA (1)	ZA826183B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6343516B1 (en) *	1998-01-16	2002-02-05	Texaco Inc.	Multiphase flow sampling using an autotraversing sample probe

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1199037A (en) *	1967-09-27	1970-07-15	Ici Ltd	Alkanolamine Derivatives
DE2503222A1 (de) *	1975-01-27	1976-07-29	Boehringer Sohn Ingelheim	Verfahren zur herstellung von 1-aryl- oxy-3-n-substituierten aminopropanderivaten
DE3015991A1 (de) *	1980-04-25	1981-11-05	C.H. Boehringer Sohn, 6507 Ingelheim	Neue 1-aryloxy-3-alkylamino-2-propanole und verfahren zur ihrer herstellung

1981
- 1981-08-26 DE DE19813133678 patent/DE3133678A1/de not_active Withdrawn
1982
- 1982-06-29 NO NO822220A patent/NO152603C/no unknown
- 1982-07-15 US US06/398,577 patent/US4442120A/en not_active Expired - Fee Related
- 1982-07-22 PH PH27614A patent/PH19705A/en unknown
- 1982-07-26 CA CA000408021A patent/CA1165324A/fr not_active Expired
- 1982-08-18 DE DE8282107536T patent/DE3267692D1/de not_active Expired
- 1982-08-18 EP EP82107536A patent/EP0073016B1/fr not_active Expired
- 1982-08-18 AT AT82107536T patent/ATE16700T1/de not_active IP Right Cessation
- 1982-08-23 FI FI822912A patent/FI75150C/fi not_active IP Right Cessation
- 1982-08-24 IL IL66633A patent/IL66633A/xx unknown
- 1982-08-24 PT PT75458A patent/PT75458A/pt unknown
- 1982-08-25 GR GR69110A patent/GR77606B/el unknown
- 1982-08-25 ES ES515245A patent/ES515245A0/es active Granted
- 1982-08-25 DK DK380482A patent/DK380482A/da not_active Application Discontinuation
- 1982-08-25 JP JP57147518A patent/JPS5859957A/ja active Pending
- 1982-08-25 ZA ZA826183A patent/ZA826183B/xx unknown
- 1982-08-25 NZ NZ201716A patent/NZ201716A/en unknown
- 1982-08-25 IE IE2047/82A patent/IE54224B1/en unknown
- 1982-08-25 KR KR8203820A patent/KR890000620B1/ko not_active Expired
- 1982-08-25 AU AU87718/82A patent/AU558338B2/en not_active Ceased
1983
- 1983-02-25 ES ES520094A patent/ES8401454A1/es not_active Expired
- 1983-02-25 ES ES520095A patent/ES520095A0/es active Granted

Also Published As

Publication number	Publication date
ES520094A0 (es)	1983-12-01
PH19705A (en)	1986-06-16
ZA826183B (en)	1984-04-25
NO152603B (no)	1985-07-15
FI75150C (fi)	1988-05-09
FI822912A0 (fi)	1982-08-23
IE54224B1 (en)	1989-07-19
IL66633A0 (en)	1982-12-31
ES8307723A1 (es)	1983-08-01
NO822220L (no)	1983-02-28
DE3267692D1 (en)	1986-01-09
DE3133678A1 (de)	1983-03-17
FI75150B (fi)	1988-01-29
ES515245A0 (es)	1983-08-01
IL66633A (en)	1986-02-28
PT75458A (de)	1982-09-01
FI822912L (fi)	1983-02-27
DK380482A (da)	1983-02-27
NO152603C (no)	1985-10-23
ES8401455A1 (es)	1983-12-01
GR77606B (fr)	1984-09-25
EP0073016B1 (fr)	1985-11-27
AU558338B2 (en)	1987-01-29
AU8771882A (en)	1983-03-03
KR890000620B1 (ko)	1989-03-22
EP0073016A1 (fr)	1983-03-02
US4442120A (en)	1984-04-10
ATE16700T1 (de)	1985-12-15
ES520095A0 (es)	1983-12-01
NZ201716A (en)	1986-02-21
ES8401454A1 (es)	1983-12-01
JPS5859957A (ja)	1983-04-09
KR840001129A (ko)	1984-03-28
IE822047L (en)	1983-02-26

Legal Events

Date	Code	Title	Description
2001-04-10	MKEX	Expiry

Publication	Publication Date	Title
IE47122B1 (en)	1983-12-28	3-indolyl-tertiary butylaminopropanols
CA1165324A (fr)	1984-04-10	1-aryloxy-3-alkylamino-propan-2-ols, et methodes pour les preparer
US4528194A (en)	1985-07-09	2-(4-Diphenylmethylpiperazinyl)-1-phenyl alkanol or their salts, a process for their production and a cerebral circulation-improving drug
US3935217A (en)	1976-01-27	Substituted pyrrolidinemethanols
US4438143A (en)	1984-03-20	1-Aryloxy-3-alkylamino-2-propanols and pharmaceutical compositions containing them
DE1940566A1 (de)	1971-02-11	1-(2-Nitrilophenoxy)-2-hydroxy-3-aethylaminopropan und dessen Salze
CA1163641A (fr)	1984-03-13	1-aryloxy-3-alkynylamino-propan-2-ols, et methodes pour les preparer
US4344964A (en)	1982-08-17	1-(Alkanoylamino-aryloxy)-2-hydroxy-3-(alkinyl-amino)-propanes and salts thereof
US4609672A (en)	1986-09-02	1-(Alkanoylamino-aryloxy)-2-hydroxy-3-(alkinyl-amino)-propanes and salts thereof
US4010158A (en)	1977-03-01	1-(2'-Ethynyl-phenoxy)-2-hydroxy-3-butylamino-propanes and salts
US4997833A (en)	1991-03-05	Aryloxy-aminoalkanes, and antihypertensive use thereof
KR850000696B1 (ko)	1985-05-15	1-(아실아미노-아릴옥시)-2-하이드록시-3-알키닐-아미노프로판의 제조방법
US4220659A (en)	1980-09-02	1-Phenoxy-2-hydroxy-3-alkynylamino-propanes and salts thereof
KR850000699B1 (ko)	1985-05-15	1-(아실아미노-아릴옥시)-2-하이드록시-3-알키닐-아미노프로판의 제조방법
KR850000698B1 (ko)	1985-05-15	1-(아실아미노-아릴옥시)-2-하이드록시-3-알키닐-아미노프로판의 제조방법
US4025646A (en)	1977-05-24	Pharmaceutical compositions containing a 1-(cyano-phenoxy)-2-hydroxy-3-hydroxyalkylamino-propane and method of use
US4016286A (en)	1977-04-05	Pharmaceutical compositions containing a 1-phenoxy-2-hydroxy-3-alkynylamino-propane and their use as adrenolytics and hypotensives
KR790001909B1 (ko)	1979-12-28	1-아릴옥시-2-하이드록시-3-알키닐아미노프로판의 제조방법
DE3030573A1 (de)	1982-03-11	2-(2-(2-hydroxy-3-tert.-butylamino-propoxy)-5-acetamidophenyl) -1,3,4-oxadiazol, verfahren zu dessen herstellung und diese verbindung enthaltende pharmazeutische zubereitung